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Volumn 72, Issue 21, 2007, Pages 8107-8110

The Wurtz-Fittig reaction in the preparation of C-silylated calixarenes

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLOXYCALIXARENE; CALIXARENE; WURTZ-FITTIG REACTION;

EID: 35348893429     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070660n     Document Type: Article
Times cited : (13)

References (47)
  • 1
    • 0004146786 scopus 로고
    • The Royal Society of Chemistry: London
    • (a) Gutsche, C. D. Calixarenes; The Royal Society of Chemistry: London, 1989.
    • (1989) Calixarenes
    • Gutsche, C.D.1
  • 3
    • 0004268367 scopus 로고    scopus 로고
    • The Royal Society of Chemistry: London
    • (c) Gutsche, C. D. Calixarenes Revisited; The Royal Society of Chemistry: London, 1998.
    • (1998) Calixarenes Revisited
    • Gutsche, C.D.1
  • 4
    • 0004266535 scopus 로고    scopus 로고
    • Mandolini, L, Ungaro, R, Eds, Imperial College Press: London
    • (d) Mandolini, L., Ungaro, R., Eds. Calixarenes in Action; Imperial College Press: London, 2000.
    • (2000) Calixarenes in Action
  • 5
    • 0004287470 scopus 로고    scopus 로고
    • Asfari, Z, Böhmer, V, Harrowfield, J, Vicens, J, Eds, Kluwer Academic Publishers: Dordrecht
    • (e) Asfari, Z.; Böhmer, V.; Harrowfield, J., Vicens, J., Eds. Calixarenes 2001; Kluwer Academic Publishers: Dordrecht, 2001.
    • (2001) Calixarenes 2001
  • 6
    • 0035793285 scopus 로고    scopus 로고
    • Anion recognition: (a) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486-516.
    • Anion recognition: (a) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486-516.
  • 7
    • 35348868830 scopus 로고    scopus 로고
    • Matthews, S. E.; Beer, P. D. In ref 1e; pp 421-439.
    • (b) Matthews, S. E.; Beer, P. D. In ref 1e; pp 421-439.
  • 19
    • 35348848023 scopus 로고    scopus 로고
    • The term Wurtz-Fittig reaction is normally used for the coupling reaction of an aryl halide with an alkyl halide in the presence of sodium. See:, 5th ed, McGraw-Hill: New York
    • The term "Wurtz-Fittig reaction" is normally used for the coupling reaction of an aryl halide with an alkyl halide in the presence of sodium. See: Smith, M. B.; March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 5th ed.; McGraw-Hill: New York, 2001; p 535.
    • (2001) Advanced Organic Chemistry: Reactions, Mechanisms, and Structure , pp. 535
    • Smith, M.B.1    March, J.2
  • 30
    • 0025732504 scopus 로고    scopus 로고
    • The shapes of calix[4]arenes are usually discussed in terms of four basic conformations: cone, partial cone, 1,2-alternate, and 1,3-alternate. For a discussion, see ref 1c, pp 41-46, and ref 1d, pp 1-10. Introduction of sufficiently large substituents onto the phenolic oxygens restricts conformational interconversion. Calixarenes 6 and 7 (as well as 3-5) are frozen in the cone conformation because of the method of preparation of starting materials 1 and 2 (see refs 13 and: (a) Groenen, L. C, Ruël, B. H. M, Casnati, A, Timmerman, P, Verboom, W, Harkema, S, Pochini, A, Ungaro, R, Reinhoudt, D. N. Tetrahedron Lett. 1991, 32, 2675-2678
    • The shapes of calix[4]arenes are usually discussed in terms of four basic conformations: cone, partial cone, 1,2-alternate, and 1,3-alternate. For a discussion, see ref 1c, pp 41-46, and ref 1d, pp 1-10. Introduction of sufficiently large substituents onto the phenolic oxygens restricts conformational interconversion. Calixarenes 6 and 7 (as well as 3-5) are frozen in the cone conformation because of the method of preparation of starting materials 1 and 2 (see refs 13 and: (a) Groenen, L. C.; Ruël, B. H. M.; Casnati, A.; Timmerman, P.; Verboom, W.; Harkema, S.; Pochini, A.; Ungaro, R.; Reinhoudt, D. N. Tetrahedron Lett. 1991, 32, 2675-2678.
  • 31
    • 0000314599 scopus 로고
    • and because of the size of the substituents on the oxygens
    • (b) Gutsche, C. D.; Reddy, P. A. J. Org. Chem. 1991, 56, 4783-4791) and because of the size of the substituents on the oxygens
    • (1991) J. Org. Chem , vol.56 , pp. 4783-4791
    • Gutsche, C.D.1    Reddy, P.A.2
  • 33
    • 35348901580 scopus 로고    scopus 로고
    • For a discussion of the NMR spectra of calix[4]arenes, see ref 16 and Ungaro, R. In ref Id; pp 1-10
    • For a discussion of the NMR spectra of calix[4]arenes, see ref 16 and Ungaro, R. In ref Id; pp 1-10.
  • 34
    • 11944260227 scopus 로고    scopus 로고
    • For references to pinched cone calix[4]arenes, see: (a) Grootenhuis, P. D. J.; Kollman, P. A.; Groenen, L. C.; Reinhoudt, D. N.; van Hummel, G. J.; Ugozzoli, F.; Andreetti, G. D. J. Am. Chem. Soc. 1990, 112, 4165-4176.
    • For references to pinched cone calix[4]arenes, see: (a) Grootenhuis, P. D. J.; Kollman, P. A.; Groenen, L. C.; Reinhoudt, D. N.; van Hummel, G. J.; Ugozzoli, F.; Andreetti, G. D. J. Am. Chem. Soc. 1990, 112, 4165-4176.
  • 43
    • 35348873968 scopus 로고    scopus 로고
    • Supporting Information to ref 19c.
    • Supporting Information to ref 19c.
  • 45
    • 35348913961 scopus 로고    scopus 로고
    • This assignment agrees with a previous COSY spectrum of a flattened cone calixarene in which a higher-field CH3 was assigned to the same propyl as a lower-field OCH2 ref 19e
    • 2 (ref 19e).
  • 46
    • 35348926475 scopus 로고    scopus 로고
    • Čajan, M.; Lhoták, P.; Lang, J.; Dvořá ková, H.; Stibor, I.; Koča, J. J. Chem. Soc., Perkin Trans. 2 2002, 1922-1929. See also ref 19h.
    • Čajan, M.; Lhoták, P.; Lang, J.; Dvořá ková, H.; Stibor, I.; Koča, J. J. Chem. Soc., Perkin Trans. 2 2002, 1922-1929. See also ref 19h.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.